2-[1-tert-butoxycarbonylamino-5-(2-chlorobenzyloxycarbonylamino)pentyl]oxazole-4-carboxylic acid | 916138-26-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-[1-tert-butoxycarbonylamino-5-(2-chlorobenzyloxycarbonylamino)pentyl]oxazole-4-carboxylic acid
• CAS: 916138-26-6
• 化学式: C₂₂H₂₈ClN₃O₇
• 分子量: 481.933
• InChiKey: ZDANWCMKSPOMTB-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.69
• 重原子数：
  33.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  139.99
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2-[1-tert-butoxycarbonylamino-5-(2-chlorobenzyloxycarbonylamino)pentyl]oxazole-4-carboxylic acid 在 2,6-二甲基吡啶 、 sodium hydroxide 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成
  参考文献：
  名称：

  Oxazole-Based Peptide Macrocycles:  A New Class of G-Quadruplex Binding Ligands

  摘要：

  Herein we report on the synthesis and DNA binding properties of a new class of water soluble oxazole-based peptide macrocycles that bind selectively to quadruplex DNA, with no detectable binding to duplex DNA. We have recently identified one quadruplex in the proto-oncogene c-kit that is suspected to act as a regulatory element for the expression of the c-kit gene. Here we provide the first example of a ligand binding to and stabilizing the c-kit quadruplex. Moreover, we show that these macrocycles show a preference for the c-kit quadruplex as compared to the human telomeric quadruplex.

  DOI：

  10.1021/ja064713e
• 作为产物：
  描述：

  methyl [N^α-(tert-butoxycarbonyl)-Nε-(2-chlorobenzylcarbonyl)-L-lysyl]-L-serinate 在 sodium hydroxide 、 三氯溴甲烷 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 4,4'-二氨基二苯乙烯-2,2'-二磺酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 2-[1-tert-butoxycarbonylamino-5-(2-chlorobenzyloxycarbonylamino)pentyl]oxazole-4-carboxylic acid
  参考文献：
  名称：

  Oxazole-Based Peptide Macrocycles:  A New Class of G-Quadruplex Binding Ligands

  摘要：

  Herein we report on the synthesis and DNA binding properties of a new class of water soluble oxazole-based peptide macrocycles that bind selectively to quadruplex DNA, with no detectable binding to duplex DNA. We have recently identified one quadruplex in the proto-oncogene c-kit that is suspected to act as a regulatory element for the expression of the c-kit gene. Here we provide the first example of a ligand binding to and stabilizing the c-kit quadruplex. Moreover, we show that these macrocycles show a preference for the c-kit quadruplex as compared to the human telomeric quadruplex.

  DOI：

  10.1021/ja064713e

文献信息

• Oxazole-Based Peptide Macrocycles:  A New Class of G-Quadruplex Binding Ligands
  作者：Katja Jantos、Raphaël Rodriguez、Sylvain Ladame、Pravin S. Shirude、Shankar Balasubramanian

  DOI：10.1021/ja064713e

  日期：2006.10.1

  Herein we report on the synthesis and DNA binding properties of a new class of water soluble oxazole-based peptide macrocycles that bind selectively to quadruplex DNA, with no detectable binding to duplex DNA. We have recently identified one quadruplex in the proto-oncogene c-kit that is suspected to act as a regulatory element for the expression of the c-kit gene. Here we provide the first example of a ligand binding to and stabilizing the c-kit quadruplex. Moreover, we show that these macrocycles show a preference for the c-kit quadruplex as compared to the human telomeric quadruplex.